ChemInform Abstract: A Compendium of Sugar Amino Acids (SAA): Scaffolds, Peptide- and Glyco-mimetics

Amino Acids DOI 10.1007/s00726-013-1521-1

REVIEW ARTICLE

A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues Martijn Risseeuw • Mark Overhand • George W. J. Fleet • Michela I. Simone

Received: 19 March 2013 / Accepted: 21 May 2013  Springer-Verlag Wien 2013

Abstract This compendium focuses on functionalised sugar amino acids (SAAs) and their 3- to 6-membered nitrogen heterocyclic and carbocyclic analogues. The main benefit of using SAAs and their related nitrogen and carbon congeners in the production of peptidomimetics and glycomimetics is that their properties can be readily altered via modification of their ring size, chemical manipulation of their numerous functional groups and fine-tuning of the stereochemical arrangement of their ring substituents. These building blocks provide access to hydrophilic and hydrophobic peptide isosteres whose physical properties allow entry to a region of chemotherapeutic space which is still under-explored by medicinal chemists. These building blocks are also important in providing amino acids whose M. Risseeuw Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, 9000 Ghent, Belgium M. Overhand (&) Bioorganic Synthesis, Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands e-mail: [email protected] G. W. J. Fleet Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK M. I. Simone (&) Department of Chemistry, School of Environmental and Life Sciences, University of Newcastle, Callaghan, NSW 2308, Australia e-mail: [email protected] M. I. Simone School of Chemistry, The University of Sydney, Eastern Avenue, Sydney, NSW 2006, Australia e-mail: [email protected]

inherent conformational bias leads to predisposition to secondary structure upon oligomerisation in relatively short sequences. These foldamers, particularly those containing x-amino acids, provide an additional opportunity to expand access to the control of structures by artificial peptides. The synthesis and biological evaluation of these building blocks in glycomimetics and peptidomimetics systems keep expanding the reach of the glycosciences to the medical sciences, provide a greater outlook onto the wide range of cellular functions of saccharides and their derivatives involved and greater insight into the nature of oligosaccharide and protein folding. Keywords Sugar amino acid  Isostere  Foldamer  Glycomimetics  Peptidomimetics  Carbohydrate

Natural SAAs Sugar amino acids (SAAs) are monosaccharide derivatives bearing an amine and a carboxylic acid functionalities (Soengas and Silva 2012; Seeberger and Werz 2005; Jensen and Brask 2005; Timmer et al. 2005; Chakraborty et al. 2002a, b, 2004a, 2005; Gruner et al. 2002a; Schweizer 2002; Knapp 1995; Lohof et al. 1999a; Dondoni and Marra 2000; Ishida and Inoue 1999). Known also as glycosamino acids, they are important in nature for their roles as antibiotics, glycosidase inhibitors, construction elements (Chakraborty et al. 2002b; Gruner et al. 2002a; Lohof et al. 1999b, 2001; Gervay-Hague and Weathers 2001) and for their involvement in inter- and intra-cellular molecular recognition events, to mention a few. Sialic acid (Fig. 1), found in almost all living organisms and located peripherally on glycoproteins and glycolipids, represents the most prominent and abundant example of the latter two.

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Fig. 1 A range of representative natural SAAs

Muramic acid also occurs widely in bacterial polysaccharides due to its involvement in peptidoglycan synthesis (Baschang 1989). Glycosaminuronic acids (Williamson and Zamenhof 1963) such as 2-acetamido-2-deoxy-glucuronic acid and 2-acetamido-2-deoxygalacturonic acid are found, respectively, as a component of bacterial cell walls (Williamson and Zamenhof 1963) and as a component of the E. coli Vi antigen (Heyns et al. 1959). Natural SAAs have also been widely found in nucleoside antibiotics (Knapp 1995) such as the naturally occurring spiro-furanoid (?)-hydantocidin (which exhibits herbicidal activity), the ezomycins (a class of complex nucleoside antibiotics, isolated from Streptomyces fermentation broths (Knapp et al. 1994; Haruyama et al. 1991; Nakajima et al. 1991; Siehl et al. 1996)), the polyoxins (Isono et al. 1969; Li et al. 2012; Isono 1988) and the nikkomycins (potent inhibitors of chitin synthetases in fungi and insects) (Isono 1988; Liao et al. 2009). Antibiotics such as amipurimycin (Wede et al. 2000; Fu¨lo¨p 2000) and miharamycins (Marcelo et al. 2008; Czernecki et al. 1996), which display strong activity against the rice blast disease caused by Pyricularia oryzae, contain a core a-

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SAA. Additionally, amipurimycin also incorporates the carbocyclic b-SAA congener cis-2-aminocyclopentane carboxylic acid (cis-2-ACPC) (Wede et al. 2000; Fu¨lo¨p 2000). The antibiotic oxetin (Barker et al. 2001; Kawahata et al. 1986) is the only naturally occurring b-AA yet reported based on an oxetane ring scaffold. It exhibits herbicidal activity and inhibits glutamine synthetase from spinach leaves (Omura et al. 1984). Other antibiotics include the more recently discovered tripropeptin (Hashizume et al. 2011) and empedopeptin (Mu¨ller et al. 2012). Siastatin B (Umezawa et al. 1974), an inhibitor of bglucuronidases, belongs to the class of SAAs which contain the amine within the pyranoid ring structure. Replacement of the endocyclic oxygen atom with a nitrogen atom leads to azasugar-based SAAs which have been found to, but are not limited to, interact with carbohydrate-active enzymes and include hydroxylated prolines (such as the antibacterial bulgecin) and pipecolic acids (Shinagawa et al. 1984; Na´varova´ et al. 2012; Kadouri-Puchot and Comesse 2005). Hydroxylated prolines have additionally been shown to influence secondary structure in peptides significantly (Takeuchi and Marshall 1998; Bellier et al. 1998).

A compendium of cyclic sugar amino acids

Synthetic amino acids H N

An important aspect of peptide chemistry involves the design, synthesis and applications of artificial amino acid building blocks. Some of the many advantages provided by the incorporation of an artificial amino acid residue in a particular peptide sequence include the introduction of a conformational bias or the achievement of a more proteolytically stable analogue. SAAs provide a set of peptide isosteres whose inherent conformational bias, chemical and physical properties can be tuned more effectively than other classes of peptidomimetics. These characteristics can be readily adjusted via the fine-tuning of the stereochemical arrangement of substituents of the sugar ring, ring size and the modification of functional groups. A number of synthetic routes to tailor-made SAA building blocks have been developed by the use of protective groups which have also allowed their incorporation into solid-phase synthesis protocols (Szabo et al. 1998; Well et al. 2003a). Besides their potential as peptidomimetics, or as glycomimetics, SAAs have been used in the design and synthesis of foldamers—peptide-like molecules which display a predisposition towards the formation of well-defined secondary structures in relatively short oligomeric sequences (Baldauf and Hofmann 2012; Martinek and Fu¨lo¨p 2012; Horne 2011; Bouillere et al. 2011; Cheng et al. 2001; Gellman 1998; Gademann et al. 1999; Hill et al. 2001; Pilsl and Reiser 2011; Roy and Balaram 2004; Seebach and Matthews 1997; Seebach et al. 2004; Seebach and Gardiner 2008; Soth and Nowick 1997). Because dense functionalisation and correct absolute stereochemical configurations are required, these building blocks are most readily synthetically derived from carbohydrate starting materials. It still is the case that novel peptidomimetics provide a driving force for the invention

Fig. 3 Top the structure of two diastereoisomeric Leuenkephalins containing a cisand a trans-furanoid d-SAAs (Chakraborty et al. 1998). Bottom design of an inhibitor of the mammalian ribonucleotide reductase (mRR) enzyme based on a trans-pyranoid e-SAA (Smith et al. 1998a)

OH HO OH H γ β α N δ H O H O

OH

O N H φ i+1

O

GUM

H N R

OH

OH

O N H

HO H γ N δ

O

R

OH β

O

H

α

H

R = Bn, iPr, CH3 O

Fig. 2 Top comparison of the cis-pyranoid d-SAA GUM with the dipeptide Gly-L-Thr (von Roedern and Kessler 1994; von Roedern et al. 1996) and bottom with the alkylated SAAs (Raunkjaer et al. 2004) that function as D-Phe-L-Thr, D-Val-L-Thr and as D-Ala-L-Thr mimic, respectively

of new drugs. The easy access to the potential candidates for such intermediates is the main intention of this paper. The original compendium on SAAs gave a restricted set of structures confined to oxygen heterocycles (Risseeuw et al. 2007a). This review is expanded to include related functionalised nitrogen heterocyclic and carbocyclic amino acid building blocks. Designed SAAs Peptidomimetics Kessler and co-workers (von Roedern and Kessler 1994) were the first to recognise that SAAs may serve as a bridge between the two worlds of glycomimetics and peptidomimetics. Thus, from this perspective, the d-SAA glucosyluronic acid methylamine (GUM) functions as a conformationally restricted dipeptide isostere. Because of the preference of the sugar core for the 4C1 chair

HO

HO O

H N

H2N

N H

O

N H

O

CO2H

H N

BocHN

O

AcHN

N H Ph

NH

N H

OH

Ph

cis (2S) trans (2R)

O

O HN

O HO2C

O

O O

O

NH O HN

AcFTLDADF OH

O

CO2H

CO2H

O

N H

O

O

Ph

O

H N O 2

Leu-enkephalin

O

OH

HO

O

H N

NH

AcHN Ph Ph

CO2H

O HO2C

NH O HN

Ph CO2H

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M. Risseeuw et al. Fig. 4 The construction of a peptidomimetic compound libraries using SAAs at the branching core (Sofia et al. 1998)

FmocHN AcO γ O

H

O

O FmocHN δ

OH or

OH H

O

O

H

OH O

OH H

O

O

20% piperidine

FmocHN

FmocHN

OP

OH H N

+ HATU, DIPEA

O

O

R1

O

H

O

O O R1

R2NCO CuCl R3

O

NHR2

O NH

O HO

O

H

O

deprotection

O

H N H

O

steps

OH R1

O

1. 20% piperidine 2. R3CO2H, HATU DIPEA

FmocHN O

OP

O

NHR2 O

O

H N H

O

O R1

or O

H N

R3 O

O

O

NHR2 O

H

O

O

H N H

O

Fig. 5 Top left a GS derivative containing a cis-furanoid dSAA. Top right Hydrogen bonding between two GS molecules. Bottom top and side views of the b-barrel-like assembly formed by six GS derivatives

OH R1

OH HN

OH O

O O

N

HN

H

HN

R

R

NH

O O

N N

O

O

H H O O

N

O

NH Ph R = (CH2)3NH2

top-view showing the cationic interior with the ornithine side-chains

conformation, which positions all substituents equatorially, the torsion angle of the SAA turn mimic between Ca and Ob, corresponding to the /i?1 torsion angle of a dipeptide (Fig. 2, top), is fixed at *180. As the a-position is

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side-view showing the hydrophobic surface areaof the exterior. The furanoid SAAs are coloured red.

functionalised as part of the sugar ring, GUM may be viewed as a very hydrophilic conformationally restricted Gly-L-Thr isostere (Fig. 2, top). From these observations, Kessler and co-workers (Gruner et al. 2002a; von Roedern

A compendium of cyclic sugar amino acids Fig. 6 The structures of some naturally occurring SAAs and their presence in many natural biopolymers

MurNAc HO

GlcNAc

L-Gal-2- NAc-4-OAcA

HO O

H O

NH HO O

R2

HO2C

n O R1

O O

O O NH

O

ManNAcA

GlcNAc

HO

HO2C O

HO

O OH HN

NH

O O

H O O

CH3 HN O O HN O

NH HO O

NH

Polysaccharide of lysoamidase

Neu5Ac

Neu5Ac

H O

O O LPS

OH H O

HO HN

NH O

H O

O

Man-2,3-diNAcA Fuc-2NAc-4NMe

HO

AcO O

HO2C O

NH

Disaccharide repeat of the peptidoglycan polymer (R1 = lipid, R2 = peptide) Glc

n OH

O HO

CO2H

O OH

OH H O

O n HO HN

O

Capped lipopolysaccharide of B. pertussis

OH CO2H

O OH

α-(2,8)-Linked sialic acid polymer

O

HO HN

NH H O

HO HN

OH CO2H

O OH

HO HN

OH CO2H

NH H O

OH CO2H

4-epi-Legionaminic acid

OH CO2H

O OH

8-epi-Legionaminic acid

Pseudaminic acid

GlcNAc

GalNAcA

GalNAcAN

NH H O

HO HN

O OH

O OH

Legionaminic acid

O

O

O NH H O

HO O H2N

HO O

HO O

HO

O

O

O

OH NH

O O

H O O

NH HO O

NH

Part of O-specific PS chain of Shigella dysenteria Fig. 7 The synthesis of amide linked SAA polymer

n O

H O

HO O

O OMe HO

OH

H O

H O

H 2N OMe HO

OH

NaOMe

HO H N H

O O OMe OH OH

D-Glycero-L-manno

heptonic acid derivative

et al. 1996) and others research groups designed a range of conformationally restricted SAA scaffolds to impart a turn bias to ‘‘linear’’ peptide mimics. For the specific structures

of these SAA building blocks, we refer to Tables 1, 2, 3, 4. For perusal, one type of alkylated SAA (Fig. 2, bottom) is illustrated (Raunkjaer et al. 2004).

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M. Risseeuw et al. Fig. 8 A helical hexameric foldamer produced by alternating SAA Neu2en and AA L-Glu

AcO

OAc H OAc O AcHN

Neuraminic acid

OAc H OAc O AcHN

DBU

Cl CO2Me

OAc

HO H 2N

Neu2en HO

OH H O

OH H O

O O HO N N H OH H

OH

OH

OH H O

OH N H O

O OH

OH

HO

N3

HO

OAc

O 2 NH

O

O NH

O HO

NHR2

H

O R1

H N

OH

O

O

O O

O

HO

N

O

O

H N

Bend-ribbon type

O

O

O

H N

O

H N

O

O O

O

O

Helical structure

O

O

O O

O OAc

AcO

OH

H N

OiPr

O

OAc

AcO

HO

O

OAc

O

O

H N

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AcO

OAc HO

R1= Phe, R2=Boc

Fig. 10 A range of pharmacologically active compounds based on SAA scaffolds

Solid phase peptide synthesis

O O

O O HO N N H OH H

O

HO

CO2H

Neu2en HO

OH

Fig. 9 Three different types of foldamers based on SAAs. The blue arrows indicate the hydrogen-bonding interactions which help stabilise the secondary structural conformations adopted by these foldamers (colour figure online)

O FmocHN

CO2Me

OAc

Neu2en HO

OH H O

O

AcO

H N O

A compendium of cyclic sugar amino acids

Many examples of SAAs incorporated in linear and cyclic peptides have been reported. Several studies have used SAAs as the common dipeptide isostere in the production of peptidic compound libraries, as depicted in Figs. 3, 4 and 5. Chakraborty compared the conformational properties of a cis- and trans-furanoid d-SAAs incorporated in a short Leu-enkephalin sequence (Fig. 3, top) and showed the induction of a turn conformation by the cisisomer. This was established spectroscopically by NMR and CD analysis, and predicted by modelling studies (Chakraborty et al. 1998). Another striking example of the use of SAAs to confer conformational bias in inhibitor design is provided by Smith et al. (Fig. 3, bottom), who showed how a highly functionalised trans-pyranoid e-SAA imparts a turn conformational bias, thus effectively mimicking the turn region of the mammalian heptapeptide AcFTLDADF-OH, an inhibitor (IC50 8.9 lM (Xu et al. 2008), Ki 15–20 lM (Smith et al. 1998a)) of mammalian ribonucleotide reductase (mRR). The SAA-containing peptidomimetic was found to inhibit the mRR with a much lower Ki of 400–500 lM (Smith et al. 1998a). Sofia et al. used SAAs as the branching point for the development of a peptidomimetic compound library on solid support (Sofia et al. 1998; Sofia 1998). Their strategy involved the following steps: the attachment of a c- or dSAA building block to an amino acid of choice, the functionalisation of a secondary hydroxyl group into a carbamate and the functionalisation of the amine group, as is outlined in Fig. 4. More recently, a variation on this theme was reported by Gomez et al. (2009) towards furanose-based carbohydrate templates. Several examples of cyclic peptides containing one or more SAAs and macrocycles composed entirely of SAAs have been reported (Well et al. 2003a; Andreini et al. 2008; Bughin et al. 2007; Hirata et al. 2007; Fleet et al. 2006; Bream et al. 2006; Fujimura et al. 2006; Menand et al. 2005; Billing and Nilsson 2005a, b; Edwards et al. 2005; Bornaghi et al. 2004; Mayes et al. 2004; Chakraborty et al. 2003; Well et al. 2000, 2003c, b; Gruner et al. 2002b; Sto¨ckle et al. 2002a, b; Chakraborty et al. 2002c; Locardi et al. 2001). One example involves the replacement of two AA residues by a cis-furanoid d-SAA in one of the turn regions of the antibiotic gramicidin S (GS) (Fig. 5) (Grotenbreg et al. 2004a). Although this GS derivative proved not to be biologically active, it revealed appealing structural features. Incorporation of the SAA introduces a hairpin twist of *45 in the cyclic b-hairpin structure of the monomeric macrocycle as shown crystallographically. Each GS analogue also binds inter-molecularly to two neighbouring molecules via four hydrogen bonds. These then form a supramolecular hexameric ensemble reminiscent of a b-barrel and possessing a cationic interior and a

hydrophobic exterior (Fig. 5). Similar pore-forming assemblies of cationic antimicrobial peptides have been suggested to occur in bio-membranes (Lazaridis et al. 2013; Semrau et al. 2010; Hartmann et al. 2010). Glycomimetics as foldamers The peptidoglycan layer is an essential and specific component of the bacterial cell wall found on the outside of the cytoplasmic membrane of almost all bacteria (Vollmer et al. 2008). The main structural feature of peptidoglycan is its composition: an ensemble of linear glycan strands, each one made up of alternating b-(1?4)-connected N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) residues, further cross-linked by short peptide sequences (Fig. 6). In Fig. 6, further examples of naturally occurring oligomeric and polymeric glycans, containing natural SAAs, are shown with their respective biological sources (Code´e et al. 2011; Schoenhofen et al. 2009; Liu et al. 2008; Lehmann et al. 2006; Caroff et al. 2000; Likhosherstov et al. 1995; Brisson et al. 1992; Kulaev et al. 1989; Knirel et al. 1988). Taking inspiration from these natural constructs, numerous carbohydrate-derived oligomers containing amide linkages in place of glycosidic linkages, now known as carbopeptoids, have been reported and their secondary structural propensities have been analysed (Szabo et al. 1998; Dane and Grinstaff 2012; Blanco et al. 2010; Timpano et al. 2008; Suhara et al. 1996a, 2002, 2006; Kyas and Feigel 2005; Durrat et al. 2004; Gervay-Hague and Weathers 2002; Liang et al. 2001; Nishimura et al. 1998; Timmers et al. 1997; Mu¨ller et al. 1995; Wessel et al. 1996; Yoshimura et al. 1976). Paulsen and co-workers were the first to report on the synthesis of a ‘‘designed’’ SAA (Heyns and Paulsen 1955). The earliest polymers entirely made of SAAs were described by Fuchs and Lehmann (1975a, b, 1976) (Fig. 7). These innovative early endeavours towards the construction of amide-linked glycomimetics involved the following steps: the multi-step conversion of a suitably protected heptonic acid derivative, the introduction of the amine functionality and the formation of polymeric materials (Fig. 7). Sialic acid is of particular interest both from a structural and a design points of view, as it has been shown that short oligomers of a-(2?8) linked sialic acid (Neu5Ac) readily adopts a helical structure (Fig. 6) (Battistel et al. 2012). Gervay-Haque et al. reported on the development of (helical) mimics of the sialic acids, oligomerised via amide linkages. Their monomeric building blocks were obtained by the subtle derivatisation of neuraminic acid (Neu) (Gregar and Gervay-Hague 2004; Gervay et al. 1997a). Another example of the use of SAA building blocks obtainable from Neu are the d/a hybrid foldamers containing alternating SAA Neu2en and AA residue L-Glu

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M. Risseeuw et al.

(Fig. 8) (Saludes and Ames 2009). A number of studies have revealed that stable foldamers could be obtained in water by oligomerisation of only six alternating AA (L-Glu)/SAA (Neu2en) residues (Saludes and Ames 2009). An example of this is provided by Saludes et al., who showed that this foldamer, in water, adopts a right-handed ˚ pitch helical conformation with 3.7 residues per turn, 7.4 A ˚ and a length of about 18.5 A. This helical structure is stabilised by both C = O…H–N backbone interactions and by another hydrogen bonding interaction between the pyranose ring oxygen and the L-Glu amide H–N. This type of construct have proven to be two to three orders of magnitude more stable than a-peptides in human blood plasma (Saludes et al. 2010). Several related SAA/AA hybrid foldamers are known which reveal further facets of the landscape of conformational preferences adopted by biopolymers (Sharma et al. 2009, 2011a; Suhara et al. 1997; Jagadeesh et al. 2009; Ramamoorthy and Gervay 1997; McDevitt and Lansbury 1996). In 1996, Ichikawa et al. reported the synthesis of an oligomer composed of four trans-b-SAA attached to a C-terminal phenylalanine ester (Fig. 9) (Suhara et al. 1996b). In several follow-up papers, it was shown that longer oligomers of this type adopt helical structures (Suhara et al. 2006), resembling the helical structures studied by Appella and coworkers (Appella et al. 1996; Seebach et al. 1996) in oligomers of b-peptides. Related structures are obtained from bamino acids having carbohydrates as their side-chains (Sharma et al. 2008; Palomo et al. 2002). Fleet demonstrated very neatly that a variety of interesting novel structures can be obtained using cis- or trans-substituted d-furanoid amino acids (Fig. 8) (Claridge et al. 1999, 2001, 2005; Long et al. 1999; Smith et al. 1998b; Smith and Fleet 1999). Molecular dynamics simulations by van Gunsteren and co-workers classified this molecular conformational variability, consistent with the experimental data (Baron et al. 2005). Ribbon- or stair-like foldameric behaviour was also displayed by oligomerisation of monomeric building block based on a b-SAA carbocyclic scaffold, such as 1-(aminomethyl)cyclopropanecarboxylic acid (Abele et al. 1999). On the other hand, short peptides of a-SAA 1-aminocyclobutane-1-carboxylic acid fold into b-turns and 310helices as demonstrated by a number of groups (Toniolo et al. 2006). These encouraging results have spurred further investigations into the synthesis of novel building blocks (Zˇukauskait_e et al. 2011). Synthesis of natural products, pharmaceutically active compounds and small molecule glycomimetics as glycosidase inhibitors SAAs have been used in the synthesis of a plethora of natural products and their analogues, including

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hydantocidin (Dondoni et al. 1994; Brandstetter et al. 1995; Renard et al. 1998), kainic acid (Cantrell et al. 1996), plusbacin (Wohlrab et al. 2007), amipurimycin, miharamycin (Casiraghi et al. 1991) and domoic acid (Clayden et al. 2005). SAAs have also been used as small molecule glycomimetics in the manipulation of the biological activities of carbohydrate-active enzymes, such as glycosidases. Their carbocyclic and especially their nitrogen congeners keep providing pharmacological leads in this area and the most remarkable class of glycosidase inhibitors to date. A few examples (Fig. 10) are provided by the wellknown c,d-SAA, marketed as Relenza (Itzstein et al. 1993), and its carbocyclic congener, marketed as Oseltamivir (Lew et al. 2000); both are neuraminidase inhibitors and used for the treatment of influenza of types A and B. Pipecolic acid derivatives (Cant and Sutherland 2012) have been used in the synthesis of a number of natural products, including synthetic peptides in HIV therapy (Copeland et al. 1990), inhibitors of the Legionella MIP Protein (Juli et al. 2011) and as potent inhibitors of bglucuronidase (Fig. 10, D-gluco and D-galacto analogues) (Yoshimura et al. 2008; Fleet et al. 1987). Aziridine derivatives, such as AziDAP, irreversibly inhibit the diaminopimelate epimerase, which is a pivotal enzyme in the biosynthesis of lysine in plants (Pillai et al. 2006, 2009). An azetidine SAA derivative that has been incorporated in marketed drug CE-178253, used in the treatment of obesity as a CB1 antagonist (Brandt et al. 2009). The L-ribono-azetidine amide was found to be very specifically a potent inhibitor of several b-hexosaminidases, thereby corroborating indications in literature that acid amides of iminosugars could provide a novel family of inhibitors for this class of enzymes (Glawar et al. 2013).

Outlook As outlined in this review, SAAs are readily accessible and versatile building blocks that have been applied to the construction of both peptido- and glycomimetics and have potential as the key constituents of new drugs. To fine-tune the properties and structures of SAA-containing molecules, subtle changes may be introduced using the corresponding nitrogen or carbocyclic analogues. Following such an approach, a plethora of related molecules emerge that may be exploited, such as in the European Innovative Medicines Initiative (IMI), in the search for new biologically active compounds. The SAAs for 3-[epoxides], 4-[oxetanes], 5-[tetrahydrofuran] and 6-[tetrahydropyran] membered rings are shown in Tables 1, 2, 3 and 4, respectively. And the corresponding nitrogen heterocycles for 3-[aziridines], 4-[azetidines], 5-[prolines] and 6-[pipecolic acids and

A compendium of cyclic sugar amino acids

morpholines] membered rings are shown in Tables 5, 6, 7, and 8, whereas analogous highly functionalised carbocyclic rings— cyclopropane, cyclobutane, cyclopentane, and cyclohexane and cycloheptane are shown in Tables 9, 10, 11 and 12, respectively.

The building block structures below only provide the tip of an iceberg in what is still a little explored section of potential chemotherapeutic space; the original review has expanded from 149 references in 2005 to 902 in 2013.

Table 1 Epoxide amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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M. Risseeuw et al. Table 1 continued

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A compendium of cyclic sugar amino acids Table 1 continued

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M. Risseeuw et al. Table 2 Oxetane amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 2 continued

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M. Risseeuw et al. Table 3 Furanoid amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 3 continued

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M. Risseeuw et al. Table 3 continued

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A compendium of cyclic sugar amino acids Table 3 continued

α

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M. Risseeuw et al. Table 3 continued

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A compendium of cyclic sugar amino acids Table 3 continued

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M. Risseeuw et al. Table 3 continued

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A compendium of cyclic sugar amino acids Table 3 continued

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M. Risseeuw et al. Table 3 continued

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A compendium of cyclic sugar amino acids Table 3 continued

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M. Risseeuw et al. Table 3 continued

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A compendium of cyclic sugar amino acids Table 4 Pyranoid amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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M. Risseeuw et al. Table 4 continued

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A compendium of cyclic sugar amino acids Table 4 continued

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M. Risseeuw et al. Table 4 continued

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A compendium of cyclic sugar amino acids Table 5 Pyranoid amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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M. Risseeuw et al. Table 6 Azetidine amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 6 continued

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M. Risseeuw et al. Table 7 Pyrrolidine amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 7 continued

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M. Risseeuw et al. Table 7 continued

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A compendium of cyclic sugar amino acids Table 7 continued

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M. Risseeuw et al. Table 8 Piperidine and morpholine amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 8 continued

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M. Risseeuw et al. Table 8 continued

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A compendium of cyclic sugar amino acids Table 8 continued

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M. Risseeuw et al. Table 9 Cyclopropyl amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 9 continued

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M. Risseeuw et al. Table 10 Cyclobutyl amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 11 Cyclopentyl amino acids (depicted with unprotected amino and carboxylic acid functionalities)

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M. Risseeuw et al. Table 11 continued

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A compendium of cyclic sugar amino acids Table 11 continued

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M. Risseeuw et al. Table 12 Cyclohexyl amino acids parent structures and their oxygenated derivatives (depicted with unprotected amino and carboxylic acid functionalities)

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A compendium of cyclic sugar amino acids Table 12 continued

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M. Risseeuw et al. Table 12 continued

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A compendium of cyclic sugar amino acids Table 12 continued

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M. Risseeuw et al. Table 12 continued

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A compendium of cyclic sugar amino acids Table 12 continued

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M. Risseeuw et al. Table 12 continued

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A compendium of cyclic sugar amino acids Table 12 continued

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M. Risseeuw et al. Table 12 continued

Acknowledgment The authors gratefully acknowledge financial support from the Leverhulme Trust. Conflict of interest of interest.

The authors declare that they have no conflict

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